Running a Google Cloud Print "server" to host "Classic" printers is a very tedious thing.
It doesn't matter whether you are running the connector in Chrome or the service which requires Chrome anyway. There are simply no tools to operate on printers or jobs in batches. Everything is one by one.
Anyway, I started out with the idea that the Google Cloud Print connector would be print driver agnostic. I have come to find out that this is not the case, and if the GCP connector doesn't like a printer driver you will be in for a hard time. And there are plenty of cases where a printer particular driver meant GCP wouldn't work, even though the printer shows online and available. You send a job
In the past in times of trouble, I've taken to cursing GCP. Now I know the problem is more than likely a print driver compatibility or configuration issue.